Journal ArticleDOI
Synthesis and antitumor activity of structural analogues of the epipodophyllotoxins
Larry L. Klein,Clinton M. Yeung,Chu Daniel T,Edith McDonald,Jacob J. Clement,Jacob J. Plattner +5 more
TLDR
The cytotoxicity of these derivatives toward several tumor cell lines is described and generally follows the structure-activity relationships known for the agent podophyllotoxin.Abstract:
Several ring-contracted analogues of the antitumor agent etoposide have been prepared. The synthesis of the simple indanyl system 3 is described along with two bicyclic systems of general structure 4 prepared through a stereoselective allylation of the keto-ester 6. A cis-fused lactone analogue 5, which is isomeric with the etoposide aglycone, has been synthesized via a dialkylation of the indene-2-carboxylate anion. Regiochemical and stereochemical results of these alkylations are described. The cytotoxicity of these derivatives toward several tumor cell lines is described and generally follows the structure-activity relationships known for the agent podophyllotoxin (2).read more
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Journal ArticleDOI
Podophyllotoxin, steganacin and combretastatin: Natural products that bind at the colchicine site of tubulin
TL;DR: A large number of antimicrotubule agents are known that bind to tubulin in vitro and disrupt microtubule assembly in vivo and in vivo, and features significant for tubulin interaction are common to these compounds and to colchicine.
Journal ArticleDOI
Antineoplastic and antiviral activities of podophyllotoxin related lignans.
Marina Gordaliza,Maria A. Castro,Maria Dolores Garcia‐Gravalos,Pilar Ruiz,José M. Miguel del Corral,Arturo San Feliciano +5 more
TL;DR: Cyclolignans, most of them derived from podophyllotoxin, have been evaluated for their antineoplastic and antiviral activities; deoxypodophyLLotoxin (1) being the most potent compound in all cases.
Journal ArticleDOI
Synthesis and evaluation of a series of benzylaniline hydrochlorides as potential cytotoxic and antimitotic agents acting by inhibition of tubulin polymerization
TL;DR: The cytotoxicities of the benzylaniline hydrochlorides correlated remarkably well with their antitubulin activities, and a relationship was found between the size of the substituent in the 4-position of the aniline ring and both antitUBulin activity and cytotoxicity.
Journal ArticleDOI
A highly enantioselective one-pot synthesis of spirolactones by an organocatalyzed Michael addition/cyclization sequence.
Silvia Sternativo,Antonella Calandriello,Ferdinando Costantino,Lorenzo Testaferri,Marcello Tiecco,Francesca Marini +5 more
TL;DR: The first highly enantioselective synthesis of spirolactones starting from racemic cyclic bketoesters and the vinyl selenone catalyzed by bifunctional cinchona-alkaloid-derived catalysts is reported.